NP-MRD: Showing NP-Card for Chiricanine D (NP0025736)

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Record Information

Version

2.0

Created at

2021-06-19 17:46:54 UTC

Updated at

2021-06-29 23:50:52 UTC

NP-MRD ID

NP0025736

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chiricanine D

Provided By

JEOL Database JEOL Logo

Description

Chiricanine D is found in Lonchocarpus chiricanus. Chiricanine D was first documented in 2001 (Ioset, J.-R., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119463D          

 55 57  0  0  0  0            999 V2000
    3.8452   -1.7962   -2.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8049   -1.2675   -3.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547   -1.9892   -4.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636   -0.2443   -3.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    0.5917   -1.8932 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4499    0.5558   -1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652    1.5744   -1.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0818    2.5918   -2.4313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7528    1.5715   -1.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1580    0.5375   -0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2941   -0.5230    0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235   -0.5044   -0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9519   -1.5980   -0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6699   -1.5970    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347   -2.6459    1.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4185   -3.9972    1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3517   -4.9672    1.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5054   -4.5973    2.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246   -3.2588    2.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7912   -2.2891    2.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5368   -3.0508   -4.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5752    0.3144   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1222    1.6224   -2.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271    3.2038   -2.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5184   -4.3124    0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6226   -0.1942    3.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  2  0  0  0  0
  7  8  1  0  0  0  0
 10  9  1  0  0  0  0
 17 18  1  0  0  0  0
 15 14  1  0  0  0  0
 19 20  1  0  0  0  0
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 14 13  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 12  1  0  0  0  0
 22 24  1  0  0  0  0
 27 24  1  0  0  0  0
 20 15  2  0  0  0  0
 22 23  1  0  0  0  0
 12  6  2  0  0  0  0
 24 25  1  1  0  0  0
 18 19  2  0  0  0  0
 24 26  1  0  0  0  0
  6  7  1  0  0  0  0
  6  5  1  0  0  0  0
  7  9  2  0  0  0  0
  5  4  1  0  0  0  0
 15 16  1  0  0  0  0
  4  2  2  3  0  0  0
 10 11  2  0  0  0  0
  2  1  1  0  0  0  0
 11 12  1  0  0  0  0
  2  3  1  0  0  0  0
 17 42  1  0  0  0  0
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 16 41  1  0  0  0  0
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  8 37  1  0  0  0  0
  9 38  1  0  0  0  0
 21 46  1  0  0  0  0
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  5 35  1  0  0  0  0
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  1 28  1  0  0  0  0
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  1 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
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   -1.7528    1.5715   -1.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1580    0.5375   -0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7246   -3.2588    2.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192119463D          

 55 57  0  0  0  0            999 V2000
    3.8452   -1.7962   -2.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8049   -1.2675   -3.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547   -1.9892   -4.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636   -0.2443   -3.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4652    1.5744   -1.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5752    0.3144   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0384   -2.3795   -0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -0.7714    1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184   -4.3124    0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741   -6.0118    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2308   -5.3522    2.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6218   -2.9678    2.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9815   -1.2490    2.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2885   -1.5558    1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699   -2.6162    0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5573   -2.2870    1.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382   -1.6417   -0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7477   -0.8640    2.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7645   -0.5465    0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7425    0.7972    1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7301    1.4190    2.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2341    0.5215    2.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6226   -0.1942    3.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  2  0  0  0  0
  7  8  1  0  0  0  0
 10  9  1  0  0  0  0
 17 18  1  0  0  0  0
 15 14  1  0  0  0  0
 19 20  1  0  0  0  0
 10 27  1  0  0  0  0
 14 13  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 12  1  0  0  0  0
 22 24  1  0  0  0  0
 27 24  1  0  0  0  0
 20 15  2  0  0  0  0
 22 23  1  0  0  0  0
 12  6  2  0  0  0  0
 24 25  1  1  0  0  0
 18 19  2  0  0  0  0
 24 26  1  0  0  0  0
  6  7  1  0  0  0  0
  6  5  1  0  0  0  0
  7  9  2  0  0  0  0
  5  4  1  0  0  0  0
 15 16  1  0  0  0  0
  4  2  2  3  0  0  0
 10 11  2  0  0  0  0
  2  1  1  0  0  0  0
 11 12  1  0  0  0  0
  2  3  1  0  0  0  0
 17 42  1  0  0  0  0
 18 43  1  0  0  0  0
 19 44  1  0  0  0  0
 20 45  1  0  0  0  0
 16 41  1  0  0  0  0
 14 40  1  0  0  0  0
 13 39  1  0  0  0  0
  8 37  1  0  0  0  0
  9 38  1  0  0  0  0
 21 46  1  0  0  0  0
 21 47  1  0  0  0  0
 22 48  1  1  0  0  0
 23 49  1  0  0  0  0
 25 50  1  0  0  0  0
 25 51  1  0  0  0  0
 25 52  1  0  0  0  0
 26 53  1  0  0  0  0
 26 54  1  0  0  0  0
 26 55  1  0  0  0  0
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
  4 34  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025736

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(\C([H])=C(/[H])C3=C([H])C([H])=C([H])C([H])=C3[H])=C1C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[C@]([H])(O[H])C(O2)(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O3/c1-16(2)10-12-19-18(13-11-17-8-6-5-7-9-17)20-14-23(26)24(3,4)27-22(20)15-21(19)25/h5-11,13,15,23,25-26H,12,14H2,1-4H3/b13-11+/t23-/m0/s1

> <INCHI_KEY>
KKSDBZMBXBGTRS-BWSGXRDBSA-N

> <FORMULA>
C24H28O3

> <MOLECULAR_WEIGHT>
364.485

> <EXACT_MASS>
364.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.30503615776358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-2,2-dimethyl-6-(3-methylbut-2-en-1-yl)-5-[(E)-2-phenylethenyl]-3,4-dihydro-2H-1-benzopyran-3,7-diol

> <ALOGPS_LOGP>
5.43

> <JCHEM_LOGP>
5.687122520666667

> <ALOGPS_LOGS>
-5.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.867019218625789

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.943047422172947

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3119976452758593

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
112.52880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-2,2-dimethyl-6-(3-methylbut-2-en-1-yl)-5-[(E)-2-phenylethenyl]-3,4-dihydro-1-benzopyran-3,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
    3.8452   -1.7962   -2.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8049   -1.2675   -3.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547   -1.9892   -4.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636   -0.2443   -3.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    0.5917   -1.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4499    0.5558   -1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652    1.5744   -1.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0818    2.5918   -2.4313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7528    1.5715   -1.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1580    0.5375   -0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2941   -0.5230    0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235   -0.5044   -0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9519   -1.5980   -0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6699   -1.5970    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347   -2.6459    1.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4185   -3.9972    1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3517   -4.9672    1.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5054   -4.5973    2.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246   -3.2588    2.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7912   -2.2891    2.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7689   -1.6565    0.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2864   -1.6480    1.1148 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8844   -2.2544   -0.0429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8166   -0.2148    1.3252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3543   -0.2159    1.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226    0.4089    2.6415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4435    0.6407    0.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151   -2.8322   -2.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267   -1.2233   -1.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8315   -1.7764   -2.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9836   -1.5872   -5.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7166   -1.9033   -5.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5368   -3.0508   -4.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625    0.0512   -3.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5752    0.3144   -1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1222    1.6224   -2.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8271    3.2038   -2.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4541    2.3684   -1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0384   -2.3795   -0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -0.7714    1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184   -4.3124    0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741   -6.0118    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2308   -5.3522    2.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6218   -2.9678    2.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9815   -1.2490    2.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2885   -1.5558    1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699   -2.6162    0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5573   -2.2870    1.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382   -1.6417   -0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7477   -0.8640    2.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7645   -0.5465    0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7425    0.7972    1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7301    1.4190    2.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2341    0.5215    2.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6226   -0.1942    3.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  2  0
  7  8  1  0
 10  9  1  0
 17 18  1  0
 15 14  1  0
 19 20  1  0
 10 27  1  0
 14 13  2  0
 11 21  1  0
 21 22  1  0
 13 12  1  0
 22 24  1  0
 27 24  1  0
 20 15  2  0
 22 23  1  0
 12  6  2  0
 24 25  1  1
 18 19  2  0
 24 26  1  0
  6  7  1  0
  6  5  1  0
  7  9  2  0
  5  4  1  0
 15 16  1  0
  4  2  2  3
 10 11  2  0
  2  1  1  0
 11 12  1  0
  2  3  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 16 41  1  0
 14 40  1  0
 13 39  1  0
  8 37  1  0
  9 38  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  1
 23 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
 26 55  1  0
  5 35  1  0
  5 36  1  0
  4 34  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.845  -1.796  -2.445  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.805  -1.268  -3.394  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.755  -1.989  -4.716  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.964  -0.244  -3.143  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.849   0.592  -1.893  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.450   0.556  -1.298  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.465   1.574  -1.601  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.082   2.592  -2.431  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.753   1.571  -1.073  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.158   0.538  -0.233  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.294  -0.523   0.063  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.024  -0.504  -0.460  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.952  -1.598  -0.131  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.670  -1.597   1.002  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.635  -2.646   1.358  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.418  -3.997   1.057  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.352  -4.967   1.433  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.505  -4.597   2.120  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.725  -3.259   2.438  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.791  -2.289   2.063  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.769  -1.657   0.944  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.286  -1.648   1.115  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.884  -2.254  -0.043  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.817  -0.215   1.325  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.354  -0.216   1.342  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.323   0.409   2.642  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.443   0.641   0.227  0.00  0.00           O+0
HETATM   28  H   UNK     0       3.615  -2.832  -2.175  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.927  -1.223  -1.520  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.832  -1.776  -2.921  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.984  -1.587  -5.381  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.717  -1.903  -5.232  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.537  -3.051  -4.559  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.262   0.051  -3.924  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.575   0.314  -1.125  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.122   1.622  -2.151  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.827   3.204  -2.548  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.454   2.368  -1.302  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.038  -2.380  -0.881  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.581  -0.771   1.705  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.518  -4.312   0.536  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.174  -6.012   1.191  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.231  -5.352   2.412  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.622  -2.968   2.978  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.982  -1.249   2.319  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.289  -1.556   1.924  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.470  -2.616   0.506  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.557  -2.287   1.963  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.738  -1.642  -0.788  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.748  -0.864   2.132  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.765  -0.547   0.381  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.742   0.797   1.501  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.730   1.419   2.767  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.234   0.522   2.664  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.623  -0.194   3.505  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   31   32   33                                             
CONECT    4    5    2   34                                                  
CONECT    5    6    4   35   36                                             
CONECT    6   12    7    5                                                  
CONECT    7    8    6    9                                                  
CONECT    8    7   37                                                       
CONECT    9   10    7   38                                                  
CONECT   10    9   27   11                                                  
CONECT   11   21   10   12                                                  
CONECT   12   13    6   11                                                  
CONECT   13   14   12   39                                                  
CONECT   14   15   13   40                                                  
CONECT   15   14   20   16                                                  
CONECT   16   17   15   41                                                  
CONECT   17   16   18   42                                                  
CONECT   18   17   19   43                                                  
CONECT   19   20   18   44                                                  
CONECT   20   19   15   45                                                  
CONECT   21   11   22   46   47                                             
CONECT   22   21   24   23   48                                             
CONECT   23   22   49                                                       
CONECT   24   22   27   25   26                                             
CONECT   25   24   50   51   52                                             
CONECT   26   24   53   54   55                                             
CONECT   27   10   24                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    5                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
CONECT   50   25                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
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   -3.4435    0.6407    0.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6151   -2.8322   -2.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7166   -1.9033   -5.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1222    1.6224   -2.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0384   -2.3795   -0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -0.7714    1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9815   -1.2490    2.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2885   -1.5558    1.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699   -2.6162    0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5573   -2.2870    1.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382   -1.6417   -0.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7477   -0.8640    2.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7645   -0.5465    0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7425    0.7972    1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7301    1.4190    2.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
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  7  8  1  0
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 17 18  1  0
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 14 13  2  0
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  4  2  2  3
 10 11  2  0
  2  1  1  0
 11 12  1  0
  2  3  1  0
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 18 43  1  0
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 16 41  1  0
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 13 39  1  0
  8 37  1  0
  9 38  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  1
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 25 52  1  0
 26 53  1  0
 26 54  1  0
 26 55  1  0
  5 35  1  0
  5 36  1  0
  4 34  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₈O₃

Average Mass

364.4850 Da

Monoisotopic Mass

364.20384 Da

IUPAC Name

(3S)-2,2-dimethyl-6-(3-methylbut-2-en-1-yl)-5-[(E)-2-phenylethenyl]-3,4-dihydro-2H-1-benzopyran-3,7-diol

Traditional Name

(3S)-2,2-dimethyl-6-(3-methylbut-2-en-1-yl)-5-[(E)-2-phenylethenyl]-3,4-dihydro-1-benzopyran-3,7-diol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C(\C([H])=C(/[H])C3=C([H])C([H])=C([H])C([H])=C3[H])=C1C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[C@]([H])(O[H])C(O2)(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H28O3/c1-16(2)10-12-19-18(13-11-17-8-6-5-7-9-17)20-14-23(26)24(3,4)27-22(20)15-21(19)25/h5-11,13,15,23,25-26H,12,14H2,1-4H3/b13-11+/t23-/m0/s1

InChI Key

KKSDBZMBXBGTRS-BWSGXRDBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lonchocarpus chiricanus	JEOL database	Ioset, J.-R., et al, J. Nat. Prod. 64, 710 (2001)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.43	ALOGPS
logP	5.69	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	8.94	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.53 m³·mol⁻¹	ChemAxon
Polarizability	42.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Ioset, J.-R., et al. (2001). Ioset, J.-R., et al, J. Nat. Prod. 64, 710 (2001). J. Nat. Prod..

Showing NP-Card for Chiricanine D (NP0025736)

MOL for NP0025736 (Chiricanine D)

3D MOL for NP0025736 (Chiricanine D)

3D SDF for NP0025736 (Chiricanine D)

3D-SDF for NP0025736 (Chiricanine D)

PDB for NP0025736 (Chiricanine D)

3D PDB for NP0025736 (Chiricanine D)

SMILES for NP0025736 (Chiricanine D)

INCHI for NP0025736 (Chiricanine D)

Structure for NP0025736 (Chiricanine D)

3D Structure for NP0025736 (Chiricanine D)